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Single Family ResidenceResidential
$621,821$381 / ft²
TopHap EstimateOur estimate of what this home would sell for today, based on nearby sales, the home's size and features, and local price trends. It is a starting point, not an appraisal.· confidence 98How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Jul 14, 2026

66 WINTER ST

HOLLISTON, MA 01746
3
Beds
1.5
Baths
1,634 ft²
Living AreaTotal finished area of the structures, from county records. Some counties include shared space like hallways or a building gym, so it may not match a listing.
0.92 ac
Lot SizeThe size of the land the home sits on, from county records.
1850
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
8
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$622K
$610K low$634K high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$7,157 (2025)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$488,500 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$291,200
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$197,300
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$582,255

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
StyleThe architectural style of the home, such as ranch or colonial.Colonial
CountyMIDDLESEX
Effective Year BuiltAn adjusted build year that accounts for condition and major remodels. A big renovation can make a home count as newer than it is.1960
Lot (acres)The size of the land the home sits on, from county records.0.92
ConstructionThe main material the home's frame and walls are built from.Stone
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Hot Water
CoolingThe type of cooling or air conditioning in the home.Yes
FireplaceWhether the home has a fireplace, and what kind.Yes
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(3)

Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

E
Placentino Elementary School
Elementary · Grades PK–2 · 0.5 mi
M
Robert H. Adams Middle SchoolA-
Middle · Grades 6–8 · 0.5 mi
H
Holliston High SchoolA
High · Grades 9–12 · 0.8 mi

District: Holliston School District

Neighborhood · ZIP 01746These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.

CrimeLocal crime compared with the rest of the country, where 100 is average. It reflects things like population density, income, and how crime gets reported.11
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.93
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.67

Index scale: 100 = US average (tick). Lower is better.

Homes occupiedThe share of homes here that someone lives in. The rest sit empty, including vacation and for-sale homes.97%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.39%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.3.1%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.4%
PopulationHow many people live in this area.15,460
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.813 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$148,945
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$184,552
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.48 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.58%

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Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.

How this home compares

66 Winter St measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.

  • Worth less than 75% of homes in Holliston 01746
  • Costs less per square foot than 73% of homes in Middlesex County
  • Has a bigger lot than 76% of homes in Middlesex County
  • Older than 98% of homes in Holliston 01746

What homes are worth in Holliston 01746

Each bar is how many homes fall in that price range. The marker is this home.

This home
$237K$1.5M

This home is worth more than 25% of homes in Holliston 01746.

How it measures up in Holliston 01746

The dot is this home. The mark in the middle is the typical home in Holliston 01746.

Estimated value$621,821
CheaperTypical $727,494Pricier

Pricier than 25% of homes nearby

Price per ft²$381
CheaperTypical $390Pricier

Pricier than 46% of homes nearby

Living area1,634 ft²
SmallerTypical 1,890 ft²Bigger

Bigger than 41% of homes nearby

Lot size0.92 ac
SmallerTypical 0.7 acBigger

Bigger than 58% of homes nearby

Year built1850
OlderTypical 1968Newer

Newer than 2% of homes nearby

How 66 Winter St ranks against every home in each area.
MeasureThis homeHolliston 01746Middlesex County
Estimated valuepricier than$621,82125% of homes27% of homes
Price per ft²pricier than$38146% of homes27% of homes
Living areabigger than1,634 ft²41% of homes41% of homes
Lot sizebigger than0.92 ac58% of homes76% of homes
Year builtnewer than18502% of homes2% of homes

About 66 Winter St

How much is 66 Winter St, Holliston, MA worth?

The TopHap Estimate for 66 Winter St, Holliston, MA is $621,821 as of Jul 14, 2026. The likely range is $609,879 to $633,763. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 66 Winter St, Holliston, MA last sell?

66 Winter St, Holliston, MA last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 66 Winter St, Holliston, MA?

66 Winter St, Holliston, MA has 3 bedrooms, 1.5 bathrooms, 1,634 square feet of living space and a 0.92-acre lot.

When was 66 Winter St, Holliston, MA built?

66 Winter St, Holliston, MA was built in 1850, making it 176 years old. It is a colonial home. The building has 2 stories.

What schools serve 66 Winter St, Holliston, MA?

66 Winter St, Holliston, MA is assigned to Placentino Elementary School (elementary); Robert H. Adams Middle School (middle), rated A-; Holliston High School (high), rated A. All sit in Holliston School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 66 Winter St, Holliston, MA compare to other homes in Holliston 01746?

Among the 5,229 homes in Holliston 01746, it is worth more than 25% of them ($621,821 against a typical $727,494), its price per square foot is higher than 46% of them ($381 against a typical $390), it is bigger than 41% of them (1,634 ft² against a typical 1,890 ft²), its lot is bigger than 58% of them (0.92 ac against a typical 0.7 ac) and it is newer than 2% of them (1850 against a typical 1968). Measured against all of Middlesex County, it is worth more than 27% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.

What are the property taxes on 66 Winter St, Holliston, MA?

The 2025 property tax bill for 66 Winter St, Holliston, MA was $7,157. The county assessed it at $488,500.

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